Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| ITF M25 Roehampton | 2023/08/11 11:25 | Oscar Weightman v Paul Jubb | 2-6,6-7 |
| ITF M25 Roehampton | 2023/08/08 15:05 | Daniel Little v Oscar Weightman | 3-6,6-7 |
| ITF M25 Roehampton | 2023/08/01 11:00 | Daniel Little v Oscar Weightman | 6-2,5-7,7-6 |
| ITF M25 Roehampton | 2023/07/18 10:00 | Billy Harris v Oscar Weightman | 6-3,6-2 |
| ITF M25 Nottingham | 2023/07/11 13:55 | Daniel Cox v Oscar Weightman | 6-1,7-5 |
| ITF M25 Ajaccio | 2023/07/05 11:50 | Patrick Brady v Oscar Weightman | 7-6,3-6,7-6 |
| ITF M25 Bakio | 2023/06/26 13:55 | Oscar Weightman v Alex Martinez | 6-7,3-6 |
| UTR Pro London | 2023/05/21 10:00 | Oscar Weightman v Luka Petrovic | 7-6,6-2 |
| ITF M25 Roehampton | 2023/08/10 14:20 | Matthew Dellavedova v Daniil Glinka | 2-6,4-6 |
| ITF M25 Roehampton | 2023/08/09 09:20 | Matthew Dellavedova v Ali Habib | 6-2,7-6 |
| Challenger Liberec | 2023/07/31 08:00 | Kirill Kivattsev v Matthew Dellavedova | 6-4,6-2 |
| Challenger Liberec | 2023/07/30 08:00 | Pawel Juszczak v Matthew Dellavedova | 5-7,2-6 |
| ITF M15 Metzingen | 2023/07/25 10:55 | Liam Gavrielides v Matthew Dellavedova | 6-2,7-5 |
| Challenger Tampere | 2023/07/17 09:00 | Matthew Dellavedova v Lorenzo Rottoli | 6-7,6-3,2-6 |
| Challenger Tampere | 2023/07/16 09:25 | Dmitry Popko v Matthew Dellavedova | 7-6,2-6,5-7 |
| Challenger Braunschweig | 2023/07/09 12:30 | Matthew Dellavedova v August Holmgren | 4-6,6-7 |